CN114621182A - Derivatization reagent, synthesis method thereof and method for analyzing monoamine neurotransmitter in situ based on MALDI-MS - Google Patents
Derivatization reagent, synthesis method thereof and method for analyzing monoamine neurotransmitter in situ based on MALDI-MS Download PDFInfo
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Abstract
The invention belongs to the field of bioanalytical chemistry, and discloses a derivatization reagent, a synthesis method thereof and a method for in-situ analysis of monoamine neurotransmitters based on MALDI-MS. The detection method is that the monoamine neurotransmitter compound and the prepared derivatization reagent are subjected to derivatization reaction, and the obtained derivatization product is detected and analyzed by using a MALDI-MS system. The novel derivatization reagent of the monoamine neurotransmitter compound, which is synthesized by the invention, can effectively aim at the derivatization of the monoamine neurotransmitter compound and improve the ionization efficiency of the monoamine neurotransmitter compound in mass spectrum. The derivatization reaction of the monoamine neurotransmitter compound and the prepared derivatization reagent has the advantages of stability, high efficiency, simple operation, low preparation cost and the like. The derivatization conditions for the derivatization reaction are carried out at room temperature without the addition of further matrix aids. Realizes the simultaneous analysis of various neurotransmitters in tissues and has high accuracy.
Description
Technical Field
The invention belongs to the field of bioanalysis chemistry, and relates to a derivatization technology of amine neurotransmitter compounds, in particular to a derivatization reagent of a monoamine neurotransmitter compound, a synthesis method thereof, and a method for analyzing the monoamine neurotransmitter in situ based on MALDI-MS.
Background
Small molecule neurotransmitters, such as catecholamine Dopamine (DA), 5-hydroxytryptamine (5-HT) and tyrosine (Tyr), are key chemicals for signal transmission between neurons. Many normal neuronal processes are associated with them, such as sleep and aging, as well as many diseases, including alzheimer's disease, Parkinson's Disease (PD), depression, drug abuse, and attention deficit hyperactivity disorder. By observing the relative abundance and distribution of these neurotransmitters in the brain, one can better understand the complex nervous system processes.
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-MS) has the advantages of high analysis speed, high signal-to-noise ratio, good signal reproducibility, wide mass range and suitability for analyzing complex samples, and has been greatly successful in rapidly analyzing biomacromolecules (nucleic acid, protein, polypeptide and the like) and polymers. These advantages ensure that MALDI technology becomes an indispensable analytical technique in the field of biochemistry, and at the same time, provide a powerful support for solving various complex biological problems. In drug development, which has the advantage of being able to detect compounds such as biomarkers, there is no use of radioisotopes or antibody labels for drugs and their metabolites, and the disadvantage of the method is that it relies on ionizable analytes.
With the increase in neurotransmitter research, the co-matrix and derivatizing reagents are expanding, allowing the detection of a wider variety of analytes. From alkali metal ions to small molecule drugs and metabolites, lipids and polypeptides. Compounds that are low in abundance and/or difficult to ionize are challenging to analyze in tissue samples because the presence of lipids and other desorption/ionization inhibitors can greatly reduce the detection limit for the target compound. In the case of neurotransmitter-like compounds, it is difficult for MS to ionize catecholamines and monoamines and their metabolites. Currently, several selective derivatization methods have been developed to increase desorption/ionization efficiency and improve the detection limit of MALDI analysis. Pyridinium salts react readily with primary amines selectively to form pyridinium cations. This derivatization method greatly improves the sensitivity of MALDI imaging for the detection of neurotransmitters. Therefore, the development of a method for derivatization of small-molecule neurotransmitters is an important prerequisite for analyzing complex nervous system processes, and related research results provide important reference information for research of neuroscience.
Because monoamine neurotransmitters are difficult to resolve/ionize in MALDI, derivatization of target compounds is required to improve their ionization efficiency and to increase the detection limit of amine neurotransmitters. Therefore, it would be a major breakthrough to develop a derivatizing agent for amine neurotransmitters that facilitates MS detection and as an effective matrix ionization to aid in its laser-induced desorption.
Disclosure of Invention
In view of the problems in the background art, the present invention provides a derivatization reagent of a monoamine neurotransmitter compound, a synthesis method thereof, and a detection method for measuring monoamine neurotransmitters based on derivatization, and provides a novel derivatization method of a monoamine neurotransmitter compound, which synthesizes a novel derivatization reagent of a monoamine compound, and aims to selectively target primary amine groups of the compound to simultaneously derive amine neurotransmitters and precursors and metabolites thereof, improve ionization efficiency of the monoamine neurotransmitter compound, improve desorption/ionization efficiency of a target analyte in a biological sample, and improve detection limit of MALDI analysis.
The invention provides a derivatization reagent synthesized by taking 3-bromothiophenol as a raw material, which is used for derivatizing a monoamine neurotransmitter compound and detecting and analyzing the amine neurotransmitter in a biological sample by using a MALDI-MS technology. Specifically, the invention provides a derivatization reagent for a monoamine neurotransmitter, which is characterized in that the structural formula of the derivatization reagent is as follows:
the second purpose of the invention is to provide a method for synthesizing a derivatization reagent of monoamine neurotransmitters, which is characterized by comprising the following steps:
step 1), uniformly stirring polyphosphoric acid, 3-bromothiophenol and ethyl 3- (4-methoxyphenyl) -3-oxopropionate, and reacting at 75-95 ℃ to obtain a mixture;
step 2), after the mixture in the step 1) is cooled to room temperature, adding ice water to quench the reaction;
step 3) extracting with dichloromethane or chloroform for three times, and combining the extract liquid to obtain an organic extract liquid;
step 4), using Na for the organic extract liquid in the step 3)2SO4Drying and filtering to obtain a crude product, and purifying the crude product by flash chromatography to obtain a purified product;
step 5), adding the product purified in the step 4) into tris (dibenzylideneacetone) dipalladium, 2-dicyclohexylphosphino-2' - (N, N-dimethylamine) -biphenyl and cesium carbonate, adding anhydrous dioxane under a closed condition, then adding diethylamine, and stirring and reacting for 12-18h at 100 ℃ to obtain a reaction mixture;
step 6), cooling the reaction mixture of step 5) to room temperature, filtering, and purifying the crude product by flash chromatography to obtain the derivatization reagent.
In the technical scheme of the invention, the mass ratio of polyphosphoric acid, 3-bromothiophenol and 3- (4-methoxyphenyl) -3-oxo ethyl propionate is 11: 1: 1.3;
preferably, in step 1), the stirring time is 1-2 h.
In the technical scheme of the invention, in the step 4), the flash chromatography adopts a flash column for purification, the flash column is a silica gel column, and the solvent is petroleum ether and dichloromethane in a volume ratio of 0-1: 1.
In the technical scheme of the invention, in the step 5), the molar ratio of the purified product, namely the dibenzylideneacetone dipalladium, the 2-dicyclohexylphosphino-2' - (N, N-dimethylamine) -biphenyl and the cesium carbonate is 1 mmol: 0.025 mmol: 0.025 mmol: 2.5 mmol;
preferably, in step 5), the ratio of the amounts of the purified product, anhydrous dioxane and diethylamine is 1:1 mmol: 5mL of: 520 μ L.
In the technical scheme of the invention, in the step 6), the flash column chromatography adopts a flash column for purification, the flash column is a silica gel column, the first flash solvent is petroleum ether and dichloromethane in a volume ratio of 0-1:1, the second flash solvent is ethyl acrylate and dichloromethane in a volume ratio of 1: 10.
the third purpose of the invention is to provide a method for analyzing monoamine neurotransmitters in situ based on MALDI-MS, wherein the method is to perform derivatization reaction on the monoamine neurotransmitters and the prepared derivatization reagent, and the obtained derivatization product is detected and analyzed by using a MALDI-MS system.
In the technical scheme of the invention, the monoamine neurotransmitters comprise dopamine, 5-hydroxytryptamine and tyrosine; preferably, the source of the monoamine neurotransmitter comprises animal brain tissue, brain microdialysis fluid and cerebrospinal fluid. The derivatization reagent is prepared into a solution by using methanol or acetonitrile as a solvent for use; the concentration of the derivatization reagent solution is 10-20 mg/mL; the pH value of the triethylamine is adjusted to 7-9.
In the technical scheme of the invention, the method for analyzing the monoamine neurotransmitters in situ based on MALDI-MS comprises the following steps:
adding methanol or acetonitrile into a sample to be detected of the monoamine neurotransmitter to obtain a monoamine neurotransmitter solution with the concentration of 0.5-2 mug/mL;
step two, adding a derivatization reagent into the monoamine neurotransmitter solution for reaction, filtering the obtained derivatization product by a filter membrane, and analyzing and detecting by using a MALDI-MS system;
preferably, in the second step, the reaction temperature is room temperature, and the reaction pH is 8-10.
In the technical scheme of the invention, the MALDI-MS analysis conditions are as follows: the mass spectrum full-scanning range is 300-700 Da/z, the laser intensity is 35%, and the positive ion reflection mode is adopted; the laser excitation source was a Nd: YAG solid-state SmartBeam laser with a wavelength of 355nm and a pulse of 2 kHz.
Compared with the prior art, the invention has the following beneficial effects:
compared with the existing neurotransmitter detection method, the method for detecting the monoamine neurotransmitters based on derivatization has the advantages that: (1) the novel derivatization reagent of the monoamine neurotransmitter compound, which is synthesized by the invention, can effectively target the derivatization of the monoamine neurotransmitter compound and improve the ionization efficiency of the monoamine neurotransmitter compound in mass spectrometry. (2) The derivatization reaction of the monoamine neurotransmitter compound and the prepared derivatization reagent has the advantages of stability, high efficiency, simple operation, low preparation cost and the like. (3) The derivatization conditions for the derivatization reaction are carried out at room temperature without the addition of further matrix aids. (4) Realizes the simultaneous analysis of various neurotransmitters in tissues and has high accuracy. Therefore, the invention has potential application value in metabonomics and disease prevention and diagnosis.
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FIG. 1 is a synthetic scheme of a derivatizing agent for a monoamine neurotransmitter compound of the present invention;
FIG. 2 is a mass spectrum of mouse brain tissue derivatized with monoamine neurotransmitters according to example 2 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to examples and comparative examples, but the embodiments of the present invention are not limited thereto. The method specifically comprises the following embodiments:
example 1
The synthesis route diagram of the derivatization reagent of the monoamine neurotransmitter compound is shown in figure 1, and the specific synthesis method comprises the following steps:
step 1) A mixture of polyphosphoric acid (PPA, 22g), 3-bromothiophenol (2g, 10.6mmol) and ethyl 3- (4-methoxyphenyl) -3-oxopropanoate (2.6g, 11.66mmol) was stirred in a beaker at 95 deg.C for 2 h.
Step 2) after the mixture of step 1) was cooled to room temperature, ice water was added to quench the reaction.
Step 3) was extracted three times with 100mL dichloromethane and the extracts were combined.
Step 4) adding Na to the organic extract in the step 3)2SO4Dried, filtered and the crude product further purified by flash column.
Step 5) the purified product (347mg,1mmol) from step 4) was charged to a test tube, and tris-dibenzylideneacetone dipalladium, (22.3mg, 0.025mmol), 2-dicyclohexylphosphino-2' - (N, N-dimethylamine) -biphenyl (9.8mg, 0.025mmol) and Cs were added2CO3(815mg，2.5mmol)。
Step 6) the tube was sealed, anhydrous dioxane (5mL) was added followed by diethylamine (520. mu.L, 5mmol), and the reaction stirred at 100 ℃ for 18 h.
And 7) cooling the reacted mixture obtained in the step 6) to room temperature, filtering, further purifying the crude product by flash chromatography, and dissolving the purified product into a derivatization reagent solution with the concentration of 20mg/mL by using methanol.
Example 2
In this example, the amine neurotransmitter is selected to be detected by using brain tissue taken from a mouse, a mass spectrometer is MALDI-TOF/MS of Ultraflextreme model, BRUKER company, and the derivatization reagent is the derivatization reagent solution with the concentration of 20mg/mL prepared in example 1, and the detection comprises the following steps:
step one, the mouse brain is added to 300mL of methanol and homogenized with a magnetic bead beater for 30 seconds.
Step two, the homogenate was centrifuged at 10000rpm for 30 minutes at 4 ℃, and the supernatant was collected and passed through a 0.20mm filter.
And step three, adding a derivatization reagent solution into the filtered supernatant, adjusting the pH to 8-10 by using triethylamine at the reaction temperature of room temperature, and then directly analyzing matrix assisted laser desorption ionization time of flight (MALDI-TOF-MS).
The matrix-assisted laser desorption ionization time-of-flight mass spectrometry analysis conditions are as follows: the mass spectrum full-scanning range is 300-700 Da/z, the laser intensity is 35%, and the positive ion reflection mode is adopted; the laser excitation source was a Nd: YAG solid-state SmartBeam laser with a wavelength of 355nm and a pulse of 2 kHz.
The mass spectrum of the mouse brain tissue after derivatization of monoamine amine neurotransmitters is shown in FIG. 2. from FIG. 2, it can be seen that the derivatization reagent can react with amine neurotransmitters and the product can peak on MALDI-MS.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (10)
1. A derivatizing agent for a monoamine neurotransmitter, said derivatizing agent having the formula:
2. a method for synthesizing a derivatization reagent of monoamine neurotransmitters, comprising the following steps:
step 1), uniformly stirring polyphosphoric acid, 3-bromothiophenol and ethyl 3- (4-methoxyphenyl) -3-oxopropionate, and reacting at 75-95 ℃ to obtain a mixture;
step 2), after the mixture in the step 1) is cooled to room temperature, adding ice water to quench the reaction;
step 3) extracting with dichloromethane or chloroform for three times, and combining the extract liquid to obtain an organic extract liquid;
step 4), using Na for the organic extract liquid in the step 3)2SO4Drying and filtering to obtain a crude product, and purifying the crude product by flash chromatography to obtain a purified product;
step 5), adding the product purified in the step 4) into tris (dibenzylideneacetone) dipalladium, 2-dicyclohexylphosphino-2' - (N, N-dimethylamine) -biphenyl and cesium carbonate, adding anhydrous dioxane under a closed condition, then adding diethylamine, and stirring and reacting for 12-18h at 100 ℃ to obtain a reaction mixture;
step 6), cooling the reaction mixture of step 5) to room temperature, filtering, and purifying the crude product by flash chromatography to obtain the derivatization reagent.
3. The method for synthesizing a derivatization reagent for a monoamine neurotransmitter according to claim 2, wherein in step 1), the mass ratio of polyphosphoric acid, 3-bromothiophenol, and ethyl 3- (4-methoxyphenyl) -3-oxopropanoate is 11: 1: 1.3;
preferably, in step 1), the stirring time is 1-2 h.
4. The method for synthesizing the derivatization reagent for the monoamine neurotransmitter according to claim 2, wherein in the step 4), the flash chromatography is performed by using a flash column, the flash column is a silica gel column, and the solvent is petroleum ether and dichloromethane in a volume ratio of 0-1: 1.
5. The method for synthesizing a derivatization reagent for a monoamine neurotransmitter according to claim 2, wherein in step 5), the molar ratio of the purified product, dipalladium tris-dibenzylideneacetone, 2-dicyclohexylphosphino-2' - (N, N-dimethylamine) -biphenyl, and cesium carbonate is 1 mmol: 0.025 mmol: 0.025 mmol: 2.5 mmol;
preferably, in step 5), the ratio of the amounts of the purified product, anhydrous dioxane and diethylamine is 1 mmol: 5mL of: 520 μ L.
6. The method for synthesizing the derivatization reagent of the monoamine neurotransmitter according to claim 2, wherein in the step 6), the flash chromatography is performed by using a flash column, the flash column is a silica gel column, the first flash solvent is petroleum ether and dichloromethane in a volume ratio of 0-1:1, the second flash solvent is ethyl acrylate and dichloromethane in a volume ratio of 1: 10.
7. a method for in situ analysis of monoamine neurotransmitters by MALDI-MS, characterized in that the method comprises derivatizing monoamine neurotransmitters with the derivatizing agent prepared according to any of claims 2 to 6, and detecting and analyzing the derivatized product by MALDI-MS.
8. The method for MALDI-MS-based in situ analysis of monoamine neurotransmitters according to claim 7, wherein said monoamine neurotransmitters include dopamine, 5-hydroxytryptamine, tyrosine; preferably, the source of the monoamine neurotransmitter comprises animal brain tissue, brain microdialysis fluid and cerebrospinal fluid. The derivatization reagent is prepared into a solution by using methanol or acetonitrile as a solvent for use; the concentration of the derivatization reagent solution is 10-20 mg/mL; the pH value of the triethylamine is adjusted to 7-9.
9. A MALDI-MS based method for in situ analysis of monoamines neurotransmitters according to claim 7, comprising the steps of:
adding methanol or acetonitrile into a sample to be detected of the monoamine neurotransmitter to obtain a monoamine neurotransmitter solution with the concentration of 0.5-2 mug/mL;
step two, adding a derivatization reagent into the monoamine neurotransmitter solution for reaction, filtering the obtained derivatization product by a filter membrane, and analyzing and detecting by using a MALDI-MS system;
preferably, in the second step, the reaction temperature is room temperature, and the reaction pH is 8-10.
10. A MALDI-MS-based method for in situ analysis of a monoamine neurotransmitter according to claim 7, wherein said MALDI-MS analysis conditions are: the mass spectrum full-scanning range is 300-700 Da/z, the laser intensity is 35%, and the positive ion reflection mode is adopted; the laser excitation source was a Nd: YAG solid-state SmartBeam laser with a wavelength of 355nm and a pulse of 2 kHz.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104678028A (en) * | 2015-02-12 | 2015-06-03 | 中国人民解放军军事医学科学院毒物药物研究所 | Pretreatment and detection method for biogen amine neurotransmitter and detection kit |
| CN105866303A (en) * | 2016-06-24 | 2016-08-17 | 曲阜师范大学 | Detecting method for determining various neurotransmitters on the basis of in situ derivation |
| CN109180638A (en) * | 2018-10-10 | 2019-01-11 | 复旦大学 | The second window of near-infrared emits Cyanine fluorochrome and its preparation method and application |
| CN112986412A (en) * | 2019-12-13 | 2021-06-18 | 中国科学院大连化学物理研究所 | Derivatization method of amino compound and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104678028A (en) * | 2015-02-12 | 2015-06-03 | 中国人民解放军军事医学科学院毒物药物研究所 | Pretreatment and detection method for biogen amine neurotransmitter and detection kit |
| CN105866303A (en) * | 2016-06-24 | 2016-08-17 | 曲阜师范大学 | Detecting method for determining various neurotransmitters on the basis of in situ derivation |
| CN109180638A (en) * | 2018-10-10 | 2019-01-11 | 复旦大学 | The second window of near-infrared emits Cyanine fluorochrome and its preparation method and application |
| CN112986412A (en) * | 2019-12-13 | 2021-06-18 | 中国科学院大连化学物理研究所 | Derivatization method of amino compound and application thereof |
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